
Vacation rentals with a pool in Middlesex County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Middlesex County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex County rentals with a pool
House rentals with a pool

Private completely fenced in property. Near beach.

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Pool House

Stunning Central E. Hampton Home w/ gunite pool.

The Hideaway

Long Island home w/ large pool

Private East Hampton Estate

New Southampton mega home with heated gunite pool!
Condo rentals with a pool

Oceanfront Condo – Incredible Spring Rates!

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

Peaceful Oasis steps from Mohegan Sun

The Vacay Villa

"Breathtaking Waterfront Water's Edge view"

A Unique Piece of Paradise, Water Front pool

Beachside Waterview 2Br Condo w/ Pool in Greenport

The N-V ...The Spa at the Norwich Inn.
Home rentals with a private pool

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

Explore the Water & Woods at a Relaxing Retreat
East Hampton Ranch with Access to Clearwater Private Beach
Enchanting Home with Large Decks and Heated Pool

Perfect Getaway at Sunny Modern Shampton Lake House
Saltbox with Separate Poolhouse in Northwest Woods
Destinations to explore
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Clinton Town Beach
- Shennecossett Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Woodmont Beach
- Horton Lane Beach
- Mystic Seaport Museum
- South Pine Creek Beach
- Wildemere Beach
- Morningside Beach
- Anchor Beach
- Sasco Hill Beach
- Fenway Beach
- East Beach
- Sasco Beach
- Lordship Beach
- Short Beach
- Milford Point Unit